N-11-Phenylundecanoyl-L-homoserine Lactone

ID: ALA447291

PubChem CID: 25258813

Max Phase: Preclinical

Molecular Formula: C21H31NO3

Molecular Weight: 345.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCCCCCCCc1ccccc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C21H31NO3/c23-20(22-19-16-17-25-21(19)24)15-11-6-4-2-1-3-5-8-12-18-13-9-7-10-14-18/h7,9-10,13-14,19H,1-6,8,11-12,15-17H2,(H,22,23)/t19-/m0/s1

Standard InChI Key:  OVBODEHQKJBHAL-IBGZPJMESA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   29.5539  -14.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7539  -14.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7088  -15.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4809  -16.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0032  -15.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6928  -16.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9917  -16.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2808  -15.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2881  -14.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5628  -16.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8520  -15.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1339  -16.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4231  -15.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7050  -16.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9942  -15.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2822  -16.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5699  -15.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8533  -16.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1409  -15.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4244  -16.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7138  -15.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9977  -16.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9931  -16.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7104  -17.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4236  -16.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  2  0
 12 13  1  0
 13 14  1  0
  3  7  1  1
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  2  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA447291

   N-[(3S)-2-oxooxolan-3-yl]-11-phenylundecanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 345.48

Molecular Weight (Monoisotopic): 345.2304

AlogP: 4.17

#Rotatable Bonds: 12

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.61

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.46

Np Likeness Score: -0.15

References

1. Oliver CM, Schaefer AL, Greenberg EP, Sufrin JR..  (2009)  Microwave synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas aeruginosa.,  52  (6): [PMID:19260689] [10.1021/jm8015377]

Source

Source(1):

• Scientific Literature